N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide | 155791-66-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide
• 英文别名: 3-amino-5-[2-(dimethylamino)ethylcarbamoyl]-1-methylpyrrole；4-amino-1-methyl-1H-pyrrole-2-carboxylic acid (2-dimethylaminoethyl)amide；4-amino-N-[2-(dimethylamino)ethyl]-1-methylpyrrole-2-carboxamide
• CAS: 155791-66-5
• 化学式: C₁₀H₁₈N₄O
• 分子量: 210.279
• InChiKey: HHHOJVUZNLQZCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 4-amino-N-[5-[2-(dimethylamino)ethylcarbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  Lee; Roldan; Haskell, Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1208 - 1213

  摘要：

  DOI：
• 作为产物：
  描述：

  1-甲基-4-硝基吡咯-2-羧酸 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 4.91h， 生成 N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide
  参考文献：
  名称：

  Lee; Roldan; Haskell, Journal of Medicinal Chemistry, 1994, vol. 37, # 8, p. 1208 - 1213

  摘要：

  DOI：

文献信息

• Synthesis of directly linked diazine isosteres of pyrrole-polyamide that photochemically cleave DNA
  作者：Chi Wi Ong、Ya-Ting Yang、Meng-Chi Liu、Keith R. Fox、Ping Hao Liu、Hung-Wei Tung

  DOI：10.1039/c1ob06803b

  日期：——

  photo-induced DNA damage upon iradiation with UV light (365 nm). Spectrophotometric and mass spectrometric identification suggest that the azo-linkage in I did not dissociate during irradiation. Moreover, compound I produced DNase I footprints with the HexB DNA fragment at AT sites, as well as some other mixed sequences (5′-ATGTCG-3′), indicative of the additional role of the diazine-linkage for interaction at

  一种 双霉素设计并合成了包含等排的二嗪连接的吡咯的模型。合成的关键步骤涉及成功的重氮化反应。4-氨基吡咯 衍生给 重氮 盐，它们与 N-甲基吡咯得到直接连接的二嗪化合物。酰胺是等位的二嗪吡咯 在紫外线（365 nm）照射下，我证明了光诱导的DNA损伤。分光光度法和质谱法鉴定表明I中的偶氮键在辐照期间未解离。此外，化合物I在AT位点的HexB DNA片段以及其他一些混合序列产生了DNase I足迹。5′-ATGTCG-3'），表明二嗪键对双链DNA相互作用的额外作用。
• 9-anilinoacridine alkylating agents
  申请人：Su Tsann-Long

  公开号：US20080176889A1

  公开（公告）日：2008-07-24

  This invention relates to 9-anilinoacridine alkylating agents, their synthesis and their use in pharmaceutical compositions for treating diseases.

  这项发明涉及9-苯胺基吖啶烷基化剂，它们的合成以及它们在治疗疾病的药物组合物中的应用。
• Antitumor AHMA Linked to DNA Minor Groove Binding Agents:  Synthesis and Biological Evaluation
  作者：Kamesh Rastogi、Jang-Yang Chang、Wen-Yu Pan、Ching-Huang Chen、Ting-Chao Chou、Li-Tzong Chen、Tsann-Long Su

  DOI：10.1021/jm0200714

  日期：2002.9.1

  DNA minor groove binder hybrid molecules, netropsin derivatives such as N-[2-(dimethylamino)ethyl]-1-methyl-4-aminopyrrolo-2-carboxamide (MePy) or its derivatives containing two units of N-methylpyrrolecarboxamide (diMePy) and bisbenzimidazole (Ho33258), were linked to the NH2 function of AHMA or to the CH2OH group of AHMA-ethylcarbamate to form AHMA-N-netropsins (13-16) and AHMA-ethylcarbamate-O-netropsins (19-22), and AHMA-bis-benzimidazole (AHMA-Ho33258, 25), respectively. These conjugates' in vitro antitumor activity, inhibition of a variety of human tumor cell growth, revealed that AHMA-ethylcarbamate-O-netropsin derivatives were more cytotoxic than AHMA-N-netropsin compounds. In the same studies, all compounds bearing MePy were more potent than those compounds linked with diMePy. Moreover, AHMA-netropsin derivatives bearing a succinyl chain as the linking spacer were more potent than those compounds having a glutaryl bridge. Among these hybrid molecules, AHMA-ethylcarbamate-O-succinyl-MePy (19) was 2- to 6-fold more cytotoxic than the parent compound AHMA (5) in various cell lines, whereas compound 25 had very poor solubility and was inactive. Studies on the inhibitory effect against topoisomerase II (Topo II) and DNA interaction of these conjugates showed no correlation between the potency of DNA binding and inhibitory activity against Topo II.
• Antitumor Imidazotetrazines. 41. Conjugation of the Antitumor Agents Mitozolomide and Temozolomide to Peptides and Lexitropsins Bearing DNA Major and Minor Groove-Binding Structural Motifs
  作者：Jill Arrowsmith、Sharon A. Jennings、Alan S. Clark、Malcolm F. G. Stevens

  DOI：10.1021/jm020936d

  日期：2002.12.1

  Carboxylic acids derived from the amido groups of the antitumor agents mitozolomide and temozolomide have been conjugated to simple amino acids and peptides by carbodiimide coupling. Solid-state peptide synthesis has been applied to link the acids to DNA major groove-binding peptidic motifs known to adopt alpha-helical conformations. Attachment of the acids to pyrrole and imidazole polyamidic lexitropsins gave a series of potential DNA minor groove- binding ligands. In vitro biological evaluation of a limited number of these novel conjugates failed to demonstrate any enhanced growth-inhibitory activity compared to the unconjugated drugs; sites of alkylation at tracts of multiple guanines were also unaffected. Attachment of additional residues at C-8 of the imidazotetrazines did not perturb the chemistry of activation of the bicyclic nucleus, and biological sequelae can be rationalized by invoking the liberation of a common, diffusible, reactive chemical intermediate, the methanediazonium ion.